
Far Southwest Side Vacations from $147
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The Latest Far Southwest Side vacation packages
Price found within the past 48 hours. Click for updated prices.

theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $320, price is now $147 per person
$147
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18/10 Exceptional! (1,001 reviews)
great staff...loved our stay.
Reviewed on Nov 22, 2025


Level Chicago – Old Town
Downtown Chicago
Price was $1,607, price is now $785 per person
$785
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
18/10 Exceptional! (380 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.
Reviewed on Nov 9, 2025


Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $396, price is now $211 per person
$211
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.4/10 Exceptional! (317 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.
Reviewed on Oct 28, 2025
Don't see what you're looking for?
See all available trips from Columbus to Far Southwest Side
View all tripsWhere to stay in Far Southwest Side
Find the best Far Southwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Far Southwest Side

Beverly
The restaurants and churches are just a few features travelers like about Beverly. If you want to do some sightseeing nearby, Martin Luther King Drive and Jones Convocation Center are a few top places to visit.
Discover the most popular places to visit in Far Southwest Side

Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Michigan Avenue
4.5/5(332 reviews)
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Navy Pier
4.5/5(4,870 reviews)
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Far Southwest Side

Skydeck - Willis Tower Admission
$44
per adult
98% of travellers recommend

Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
84% of travellers recommend

Wendella's 90-min Chicago River Architecture Tour
$45
per adult
94% of travellers recommend
Far Southwest Side Hotel Deals

Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $102 total per night from Dec 21 to Dec 22
$102 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (5,275 reviews)
It’s conveniently close to several tourist attractions. Highly recommended! 💯
Reviewed on Nov 20, 2025

Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $145 total per night from Dec 21 to Dec 22
$145 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (2,074 reviews)
The hotel was a beautiful gem. Our room with 2 queen beds & 2 barrooms was huge! Great place to stay in the city, walking distance to attractions & bars & restaurants.
Reviewed on Nov 21, 2025

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $98 total per night from Dec 7 to Dec 8
$98 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (3,342 reviews)
Accommodated early arrival and held my bags after checkout
Reviewed on Nov 21, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find the Best Far Southwest Side Vacation Packages
Far Southwest Side Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.




















